Retracted: catena-Poly[[(acetato-κO)(1,10-phenanthroline-κ²N,N′)cobalt(II)]-μ-acetato-κ²O:O′]

The title compound, [Co(C₂H₃O₂)₂(C₁₂H₈N₂)]_n, is a polymeric complex involving bridging of Co^II ions by single syn-anti acetate ligands. Each Co atom is five-coordinated by two 1,10-phenanthroline N atoms and three O atoms of acetate ligands within a bipyramidal coordination geometry. In the crystal structure, C—H...O hydrogen bonds result in the formation of a polymeric ribbon structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.127
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT362_ALERT_2_B Short  C(sp3)-C(sp2) Bond  C13    -   C14    ...       1.22 Ang.
PLAT362_ALERT_2_B Short  C(sp3)-C(sp2) Bond  C15    -   C16    ...       1.23 Ang.
PLAT411_ALERT_2_B Short Inter H...H Contact  H5     ..  H14B    ..       2.02 Ang.
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H2     ..  H16A    ..       1.98 Ang.
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H5     ..  H16B    ..       2.01 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O3      ..       2.82 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C15     ..       5.49 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O1      ..       9.50 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O2      ..       7.34 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   N1      ..       9.12 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   N2      ..       8.56 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (9)       2.26
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Aromatic polycyclic compounds, such as phenanthroline, quinoline and benzimidazole, are one of the most important classes of biological ligands and the coordinations of metal-aromatic polycyclic compounds are of critical importance in biological systems, organic materials and coordination chemistry (Wu et al., 2003; Pan & Xu, 2004; Liu et al., 2004; Li et al., 2005). As a bidentate flexible ligand, carboxyl groups compounds are also good ligands with excellent coordination capabilities to generate mono-, bi- or trinuclear complexes, which are commonly used as precursors for the formation of supramolecular architectures (McCann et al., 1996; McCann et al., 1995; Wai et al., 1990; Yaghi et al., 1996; Min & Lee 2002; Maira et al., 2001). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). It has an inversion centre midway between the two Co^II ions, which are bridged by two bidentate and two monodentate carboxyl groups. Each Co atom is five-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and three O atoms of acetate ligands. The Co—O and Co—N bonds are in the range of [1.941 (2)–2.320 (2) Å] and [1.984 (2)–2.008 (3) Å], respectively (Table 1).

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2, Fig. 2) result in the formation of a polymeric ribbon structure.

Related literature

For related literature, see: Desiraju (1995, 1997); Braga et al. (1998); Wu et al. (2003); Pan & Xu (2004); Liu et al. (2004); Li et al. (2005); McCann et al. (1995, 1996); Wai et al. (1990); Yaghi et al. (1996); Min & Lee (2002); Maira et al. (2001). For bond-length data, see: Allen et al. (1987).

S2. Experimental

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Cobalt (II) nitrate hexahydrate (291.1 mg, 1 mmol), phen (180.2 mg, 1 mmol), acetic acid (120.1 mg, 2 mmol), ammonia (4 ml, 0.5 mol/l) and distilled water (10 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small pink crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å, for aromatic and methyl H atoms and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): -x + 3/2, y + 1/2, -z + 1/2].
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

catena-Poly[[(acetato-κO)(1,10-phenanthroline-κ²N,N')cobalt(II)]-µ- acetato-κ²O:O']

Crystal data

[Co(C2H3O2)2(C12H8N2)]	F(000) = 732
Mr = 357.22	Dx = 1.788 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 5524 reflections
a = 8.6864 (17) Å	θ = 2.3–28.0°
b = 9.183 (2) Å	µ = 1.32 mm^−1
c = 17.0024 (11) Å	T = 273 K
β = 101.897 (4)°	Prism, pink
V = 1327.1 (4) Å^3	0.41 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2779 independent reflections
Radiation source: fine-focus sealed tube	2349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.617, Tmax = 0.774	k = −11→11
8683 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0915P)^2 + 0.5483P] where P = (Fo^2 + 2Fc^2)/3
2779 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.69 e Å^−3
2 restraints	Δρmin = −0.51 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.66505 (4)	0.92788 (4)	0.803184 (19)	0.03316 (17)
O1	0.6876 (3)	0.7352 (2)	0.75202 (12)	0.0458 (5)
O2	0.5483 (3)	1.0049 (3)	0.70205 (13)	0.0530 (6)
O3	0.6215 (3)	0.5047 (2)	0.74862 (15)	0.0528 (6)
O4	0.3286 (3)	1.0280 (4)	0.62132 (17)	0.0706 (8)
N1	0.6077 (3)	1.0939 (3)	0.86847 (16)	0.0412 (5)
N2	0.7957 (3)	0.8671 (3)	0.90793 (14)	0.0393 (5)
C1	0.5195 (4)	1.2113 (4)	0.8471 (2)	0.0489 (7)
H1	0.4800	1.2274	0.7927	0.059*
C2	0.4838 (4)	1.3105 (4)	0.9017 (2)	0.0546 (8)
H2	0.4234	1.3922	0.8837	0.065*
C3	0.5366 (4)	1.2887 (4)	0.9811 (2)	0.0531 (8)
H3	0.5101	1.3531	1.0184	0.064*
C4	0.6330 (3)	1.1659 (3)	1.00699 (18)	0.0424 (6)
C5	0.6983 (4)	1.1338 (4)	1.0880 (2)	0.0515 (8)
H5	0.6746	1.1926	1.1284	0.062*
C6	0.7946 (4)	1.0188 (4)	1.10743 (19)	0.0495 (7)
H6	0.8355	0.9995	1.1614	0.059*
C7	0.8360 (4)	0.9255 (3)	1.04817 (18)	0.0416 (6)
C8	0.9430 (4)	0.8077 (4)	1.06368 (18)	0.0474 (7)
H8	0.9931	0.7862	1.1162	0.057*
C9	0.9723 (4)	0.7262 (4)	1.0018 (2)	0.0505 (7)
H9	1.0434	0.6493	1.0117	0.061*
C10	0.8957 (4)	0.7581 (3)	0.92380 (19)	0.0466 (7)
H10	0.9154	0.7011	0.8817	0.056*
C11	0.7671 (3)	0.9514 (3)	0.96843 (17)	0.0370 (6)
C12	0.6651 (3)	1.0725 (3)	0.94750 (18)	0.0367 (6)
C13	0.6166 (3)	0.6284 (3)	0.77790 (16)	0.0339 (5)
C14	0.5457 (4)	0.6525 (3)	0.83168 (19)	0.0441 (7)
H14A	0.4484	0.5995	0.8215	0.066*
H14B	0.5243	0.7549	0.8336	0.066*
H14C	0.6088	0.6222	0.8822	0.066*
C15	0.4032 (3)	0.9782 (3)	0.68379 (16)	0.0366 (6)
C16	0.3456 (4)	0.9001 (5)	0.7293 (2)	0.0565 (9)
H16A	0.2335	0.9124	0.7181	0.085*
H16B	0.3881	0.9271	0.7840	0.085*
H16C	0.3705	0.8001	0.7212	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0395 (2)	0.0320 (2)	0.0266 (2)	0.00247 (13)	0.00361 (16)	0.00086 (13)
O1	0.0559 (12)	0.0429 (11)	0.0393 (10)	−0.0051 (10)	0.0115 (9)	−0.0023 (9)
O2	0.0501 (12)	0.0604 (16)	0.0443 (12)	−0.0060 (11)	−0.0001 (10)	0.0126 (11)
O3	0.0516 (12)	0.0417 (12)	0.0654 (14)	−0.0049 (10)	0.0127 (11)	−0.0152 (11)
O4	0.0609 (15)	0.0780 (18)	0.0622 (16)	−0.0064 (14)	−0.0117 (13)	0.0198 (15)
N1	0.0439 (12)	0.0375 (12)	0.0420 (13)	0.0019 (10)	0.0083 (11)	0.0042 (10)
N2	0.0454 (12)	0.0359 (12)	0.0359 (11)	0.0016 (10)	0.0066 (10)	−0.0015 (10)
C1	0.0508 (16)	0.0449 (17)	0.0500 (16)	0.0058 (14)	0.0078 (14)	0.0047 (14)
C2	0.0521 (17)	0.0441 (17)	0.067 (2)	0.0122 (14)	0.0108 (16)	0.0045 (16)
C3	0.0532 (17)	0.0442 (18)	0.065 (2)	0.0079 (14)	0.0206 (16)	−0.0054 (15)
C4	0.0434 (14)	0.0413 (15)	0.0456 (15)	−0.0025 (12)	0.0161 (12)	−0.0028 (12)
C5	0.0588 (18)	0.0550 (19)	0.0451 (16)	−0.0029 (16)	0.0206 (15)	−0.0098 (14)
C6	0.0535 (17)	0.0598 (19)	0.0356 (14)	0.0007 (15)	0.0100 (13)	−0.0008 (14)
C7	0.0453 (15)	0.0425 (16)	0.0366 (14)	−0.0051 (12)	0.0077 (12)	0.0027 (11)
C8	0.0528 (16)	0.0476 (17)	0.0387 (14)	0.0008 (14)	0.0025 (13)	0.0067 (13)
C9	0.0538 (17)	0.0405 (16)	0.0538 (17)	0.0087 (13)	0.0032 (14)	0.0043 (14)
C10	0.0517 (16)	0.0391 (15)	0.0471 (16)	0.0065 (13)	0.0059 (13)	−0.0051 (13)
C11	0.0411 (14)	0.0334 (13)	0.0373 (14)	−0.0032 (11)	0.0097 (11)	0.0001 (11)
C12	0.0376 (13)	0.0348 (14)	0.0385 (14)	−0.0030 (10)	0.0097 (11)	0.0024 (11)
C13	0.0343 (12)	0.0321 (13)	0.0344 (13)	0.0004 (10)	0.0048 (10)	−0.0030 (11)
C14	0.0571 (17)	0.0342 (14)	0.0520 (16)	−0.0042 (12)	0.0368 (15)	−0.0044 (12)
C15	0.0378 (13)	0.0356 (13)	0.0338 (13)	−0.0001 (11)	0.0012 (11)	0.0002 (11)
C16	0.0439 (16)	0.088 (3)	0.0378 (16)	−0.0182 (16)	0.0085 (13)	0.0191 (17)

Geometric parameters (Å, º)

Co1—O1	1.999 (2)	C4—C5	1.408 (5)
Co1—O2	1.941 (2)	C5—C6	1.346 (5)
Co1—O3^i	2.320 (2)	C5—H5	0.9300
Co1—N1	2.008 (3)	C6—C7	1.424 (5)
Co1—N2	1.984 (2)	C6—H6	0.9300
O1—C13	1.283 (4)	C7—C11	1.385 (4)
O2—C15	1.259 (4)	C7—C8	1.415 (5)
O3—C13	1.245 (4)	C8—C9	1.357 (5)
O3—Co1^ii	2.320 (2)	C8—H8	0.9300
O4—C15	1.214 (4)	C9—C10	1.387 (5)
N1—C1	1.329 (4)	C9—H9	0.9300
N1—C12	1.348 (4)	C10—H10	0.9300
N2—C10	1.316 (4)	C11—C12	1.421 (4)
N2—C11	1.351 (4)	C13—C14	1.223 (4)
C1—C2	1.381 (5)	C14—H14A	0.9600
C1—H1	0.9300	C14—H14B	0.9600
C2—C3	1.348 (5)	C14—H14C	0.9600
C2—H2	0.9300	C15—C16	1.234 (4)
C3—C4	1.419 (5)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C12	1.398 (4)	C16—H16C	0.9600
O1—Co1—O2	91.00 (10)	C11—C7—C8	116.6 (3)
O1—Co1—O3^i	86.94 (9)	C11—C7—C6	118.0 (3)
O2—Co1—O3^i	82.25 (9)	C8—C7—C6	125.4 (3)
O1—Co1—N1	165.97 (10)	C9—C8—C7	119.9 (3)
O1—Co1—N2	93.00 (9)	C9—C8—H8	120.1
O2—Co1—N1	93.96 (11)	C7—C8—H8	120.1
O2—Co1—N2	174.47 (10)	C8—C9—C10	119.7 (3)
O3—Co1—N1^i	138.62 (4)	C8—C9—H9	120.2
O3—Co1—N2^i	125.59 (5)	C10—C9—H9	120.2
N1—Co1—N2	83.03 (10)	N2—C10—C9	121.5 (3)
C13—O1—Co1	115.45 (18)	N2—C10—H10	119.2
C15—O2—Co1	117.46 (19)	C9—C10—H10	119.2
C13—O3—Co1^ii	121.71 (18)	N2—C11—C7	122.5 (3)
C1—N1—C12	117.7 (3)	N2—C11—C12	117.4 (3)
C1—N1—Co1	131.2 (2)	C7—C11—C12	120.0 (3)
C12—N1—Co1	110.95 (19)	N1—C12—C4	123.0 (3)
C10—N2—C11	119.8 (3)	N1—C12—C11	116.6 (3)
C10—N2—Co1	129.0 (2)	C4—C12—C11	120.4 (3)
C11—N2—Co1	111.18 (19)	C14—C13—O3	121.9 (3)
N1—C1—C2	123.3 (3)	C14—C13—O1	118.0 (3)
N1—C1—H1	118.4	O3—C13—O1	120.1 (3)
C2—C1—H1	118.4	C13—C14—H14A	109.5
C3—C2—C1	119.8 (3)	C13—C14—H14B	109.5
C3—C2—H2	120.1	H14A—C14—H14B	109.5
C1—C2—H2	120.1	C13—C14—H14C	109.5
C2—C3—C4	119.1 (3)	H14A—C14—H14C	109.5
C2—C3—H3	120.5	H14B—C14—H14C	109.5
C4—C3—H3	120.5	O4—C15—C16	123.8 (3)
C12—C4—C5	118.6 (3)	O4—C15—O2	118.0 (3)
C12—C4—C3	117.1 (3)	C16—C15—O2	118.3 (3)
C5—C4—C3	124.3 (3)	C15—C16—H16A	109.5
C6—C5—C4	120.7 (3)	C15—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C4—C5—H5	119.7	C15—C16—H16C	109.5
C5—C6—C7	122.2 (3)	H16A—C16—H16C	109.5
C5—C6—H6	118.9	H16B—C16—H16C	109.5
C7—C6—H6	118.9

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4^iii	0.93	2.51	3.327 (4)	147
C10—H10···O2^ii	0.93	2.36	3.263 (4)	164

Symmetry codes: (ii) −x+3/2, y−1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2.